CA2458230A1 - Method and composition for treatment of ocular hypertension and glaucoma - Google Patents
Method and composition for treatment of ocular hypertension and glaucoma Download PDFInfo
- Publication number
- CA2458230A1 CA2458230A1 CA002458230A CA2458230A CA2458230A1 CA 2458230 A1 CA2458230 A1 CA 2458230A1 CA 002458230 A CA002458230 A CA 002458230A CA 2458230 A CA2458230 A CA 2458230A CA 2458230 A1 CA2458230 A1 CA 2458230A1
- Authority
- CA
- Canada
- Prior art keywords
- keto
- prostaglandin compound
- dihydro
- alkyl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- 208000010412 Glaucoma Diseases 0.000 title claims abstract description 14
- 206010030043 Ocular hypertension Diseases 0.000 title claims abstract description 14
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- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- -1 13,14-dihydro-15-keto-prostaglandin compound Chemical class 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000001931 aliphatic group Chemical group 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000004043 oxo group Chemical group O=* 0.000 claims description 13
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
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- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
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- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 239000001656 lutein Substances 0.000 description 1
- 229960005375 lutein Drugs 0.000 description 1
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- 235000012680 lutein Nutrition 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical compound COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000003956 methylamines Chemical class 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- AIAKLPAJNLBVEA-UHFFFAOYSA-N n-[2-(2-benzamidophenoxy)phenyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC=C1 AIAKLPAJNLBVEA-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
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- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000010409 propane-1,2-diol alginate Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
- CBOMORHDRONZRN-QLOYDKTKSA-N prostaglandin E3 Chemical compound CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O CBOMORHDRONZRN-QLOYDKTKSA-N 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229940010747 sodium hyaluronate Drugs 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- RYYVLZVUVIJVGH-UHFFFAOYSA-N trimethylxanthine Natural products CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
- A61K31/5575—Eicosanoids, e.g. leukotrienes or prostaglandins having a cyclopentane, e.g. prostaglandin E2, prostaglandin F2-alpha
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31411001P | 2001-08-23 | 2001-08-23 | |
| US60/314,110 | 2001-08-23 | ||
| PCT/JP2002/008446 WO2003018025A1 (en) | 2001-08-23 | 2002-08-22 | Method and composition for treatment of ocular hypertension and glaucoma |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2458230A1 true CA2458230A1 (en) | 2003-03-06 |
Family
ID=23218598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002458230A Abandoned CA2458230A1 (en) | 2001-08-23 | 2002-08-22 | Method and composition for treatment of ocular hypertension and glaucoma |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20030060511A1 (ko) |
| EP (1) | EP1420793A1 (ko) |
| JP (1) | JP2004521960A (ko) |
| KR (1) | KR20040029012A (ko) |
| CN (1) | CN1575178A (ko) |
| AR (1) | AR036276A1 (ko) |
| BR (1) | BR0205932A (ko) |
| CA (1) | CA2458230A1 (ko) |
| MX (1) | MXPA04001604A (ko) |
| NO (1) | NO20031779L (ko) |
| WO (1) | WO2003018025A1 (ko) |
| ZA (1) | ZA200302911B (ko) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003215820A1 (en) * | 2002-03-28 | 2003-10-13 | Sucampo Ag | Method for treating ocular hypertension and glaucoma |
| US20040225014A1 (en) * | 2003-02-14 | 2004-11-11 | Sucampo Ag | Method for treating ocular hypertension and glaucoma |
| US10206813B2 (en) | 2009-05-18 | 2019-02-19 | Dose Medical Corporation | Implants with controlled drug delivery features and methods of using same |
| KR20140035363A (ko) | 2011-04-07 | 2014-03-21 | 수캄포 아게 | 안정피로 치료 방법 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932389A (en) * | 1974-12-11 | 1976-01-13 | Pfizer Inc. | 2-Descarboxy-2-(tetrazol-5-yl)-11-desoxy-15-substituted-.omega.-pentanorprostaglandins |
| US5212200A (en) * | 1987-09-18 | 1993-05-18 | R-Tech Ueno, Ltd. | Ocular hypotensive agents |
| US5321128A (en) * | 1988-09-06 | 1994-06-14 | Kabi Pharmacia Ab | Prostaglandin derivatives for the treatment of glaucoma or ocular hypertension |
| ES2213504T1 (es) * | 1988-09-06 | 2004-09-01 | Pfizer Health Ab | Derivados de prostaglandina para el tratamiento del glaucoma o hipertension ocular. |
| US5296504A (en) * | 1988-09-06 | 1994-03-22 | Kabi Pharmacia | Prostaglandin derivatives for the treatment of glaucoma or ocular hypertension |
| US6187813B1 (en) * | 1990-04-10 | 2001-02-13 | Pharmacia & Upjohn Aktiebolag | Prostaglandin derivatives for the treatment of glaucoma or ocular hypertension |
| EP0580268B1 (en) * | 1988-10-01 | 1998-01-14 | R-Tech Ueno Ltd. | Ocular hypotensive agents |
| US5194429A (en) * | 1988-10-01 | 1993-03-16 | K.K. Ueno Seiyaku Oyo Kenkyujo | Ocular hypotensive agents |
| TW224942B (ko) * | 1990-04-04 | 1994-06-11 | Adka Ueno Kk | |
| DE69105349T2 (de) * | 1990-05-22 | 1995-04-06 | Ueno Seiyaku Oyo Kenkyujo Kk | Behandlung von intraocularem Druck mit einer synergistischen Kombination zur ophthalmischen Verwendung. |
| CA2046069C (en) * | 1990-07-10 | 2002-04-09 | Ryuji Ueno | Treatment of inflammatory diseases with 15-keto-prostaglandin compounds |
| AU687906B2 (en) * | 1993-12-15 | 1998-03-05 | Alcon Laboratories, Inc. | Use of certain prostaglandin analogues to treat glaucoma and ocular hypertension |
| TW420611B (en) * | 1995-03-10 | 2001-02-01 | R Tech Ueno Ltd | Pharmaceutical composition containing prostanoic acid compounds for the treatment of optic nerve disorder |
| AU7680096A (en) * | 1995-12-22 | 1997-07-17 | Alcon Laboratories, Inc. | Combinations of dp and fp type prostaglandins for lowering iop |
| US6458836B1 (en) * | 2000-03-16 | 2002-10-01 | Sucampo, A.G. | Treatment of ocular hypertension and glaucoma |
| US20020035148A1 (en) * | 2000-07-20 | 2002-03-21 | Ryuji Ueno | Treatment of ocular hypertension |
-
2002
- 2002-08-22 BR BR0205932-0A patent/BR0205932A/pt not_active Application Discontinuation
- 2002-08-22 CA CA002458230A patent/CA2458230A1/en not_active Abandoned
- 2002-08-22 CN CNA028209214A patent/CN1575178A/zh active Pending
- 2002-08-22 MX MXPA04001604A patent/MXPA04001604A/es unknown
- 2002-08-22 WO PCT/JP2002/008446 patent/WO2003018025A1/en not_active Application Discontinuation
- 2002-08-22 KR KR10-2004-7002670A patent/KR20040029012A/ko not_active Application Discontinuation
- 2002-08-22 JP JP2003522543A patent/JP2004521960A/ja not_active Withdrawn
- 2002-08-22 EP EP02760691A patent/EP1420793A1/en not_active Withdrawn
- 2002-08-22 AR ARP020103150A patent/AR036276A1/es unknown
- 2002-08-22 US US10/224,923 patent/US20030060511A1/en not_active Abandoned
-
2003
- 2003-04-14 ZA ZA200302911A patent/ZA200302911B/xx unknown
- 2003-04-22 NO NO20031779A patent/NO20031779L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA04001604A (es) | 2004-07-08 |
| NO20031779D0 (no) | 2003-04-22 |
| WO2003018025A1 (en) | 2003-03-06 |
| CN1575178A (zh) | 2005-02-02 |
| KR20040029012A (ko) | 2004-04-03 |
| ZA200302911B (en) | 2003-10-14 |
| AR036276A1 (es) | 2004-08-25 |
| BR0205932A (pt) | 2004-02-17 |
| NO20031779L (no) | 2003-04-22 |
| JP2004521960A (ja) | 2004-07-22 |
| US20030060511A1 (en) | 2003-03-27 |
| EP1420793A1 (en) | 2004-05-26 |
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